NSC45356

Base Information

• Chemical Name: NSC45356
• CAS No.: 3775-60-8
• Molecular Formula: C2H3 N3 O
• Molecular Weight: 85.0653
• Hs Code.: 2934999090
• Mol file: 3775-60-8.mol

Synonyms:1,3,4-Oxadiazole,2-amino- (6CI,7CI,8CI); 2-Amino-1,3,4-oxadiazole; 5-Imino-D2-1,3,4-oxadiazoline; NSC 45356

Chemical Property of NSC45356

Chemical Property:

• Vapor Pressure: 0.247mmHg at 25°C
• Melting Point: 156 °C
• Boiling Point: 205.6°C at 760 mmHg
• PKA: -0.75±0.10(Predicted)
• Flash Point: 78.2°C
• PSA: 64.94000
• Density: 1.395g/cm³
• LogP: 0.23300
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

97% ^*data from raw suppliers

1,3,4-oxadiazol-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: NSC45356 (2-amino-1,3,4-oxadiazole) is a pharmacophoric scaffold notable for its metabolic stability and hydrogen-bonding properties, making it valuable in medicinal chemistry. NSC45356 can be efficiently synthesized via cyclization of thiosemicarbazides, a method that outperforms semicarbazide-based routes, yielding high-purity derivatives (78–99%) in a convenient two-step, one-pot process. Its structural versatility allows for diverse biological applications.

Technology Process of NSC45356

There total 9 articles about NSC45356 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

2-Amino-5-acetyl-1,3,4-oxadiazol (74949-72-7) + 1,2-diamino-benzene (95-54-5) → 1,3,4-oxadiazol-2-amine (3775-60-8) + 2-Methyl-1H-benzimidazole (615-15-6) + 2-Methyl-3-semicarbazido-chinoxalin (79015-02-4)

Guidance literature:

With hydrogenchloride; In ethanol; for 0.5h; Heating;

Reference yield:

bromocyane (506-68-3) + formic acid hydrazide (624-84-0) → 1,3,4-oxadiazol-2-amine (3775-60-8)

Guidance literature:

Reference yield:

5-amino[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (4970-53-0) → 1,3,4-oxadiazol-2-amine (3775-60-8)

Guidance literature:

With sodium hydroxide; In water; for 0.0833333h;

upstream raw materials:

bromocyane

formic acid hydrazide

2-Amino-5-acetyl-1,3,4-oxadiazol

1,2-diamino-benzene

Downstream raw materials:

1-[1,3,4]oxadiazol-2-yl-3-phenyl-urea

(triphenyl-λ⁵-phosphanylidene)-[1,3,4]oxadiazol-2-yl-amine

4-[(2R)-1-(1,3,4-oxadiazol-2-ylamino)-1-oxopropan-2-yl]phenyl trifluoromethanesulfonate

Refernces

Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles

10.1021/jo0618730

The study presents a novel and efficient method for synthesizing 2-amino-1,3,4-oxadiazoles, which are important pharmacophores due to their metabolic stability and hydrogen bonding capabilities. The key chemicals involved include thiosemicarbazides, which are prepared by acylating hydrazides with isothiocyanates. The thiosemicarbazides are then cyclized using tosyl chloride and pyridine in THF under reflux conditions to form the desired 2-amino-1,3,4-oxadiazoles. This method consistently outperforms the analogous semicarbazide cyclization, yielding 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in high yields (78-99%). The study highlights the superior reactivity of thiosemicarbazides compared to semicarbazides in this cyclization process, and it demonstrates the generality of this approach with various substituents. Additionally, the study shows that the thiosemicarbazides can be used directly from the crude acylation reaction mixture without purification, making the synthesis a convenient two-step, one-pot process. This method provides an efficient and robust route for the preparation of a wide variety of 2-amino-1,3,4-oxadiazoles, which are valuable in medicinal chemistry for their diverse biological activities.

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